20 Questions with John Flanagan

As CEO of CareerSource Tampa Bay, Flanagan works closely with business, government and educational entities to find workforce solutions for the more than 1.5 million Hillsborough County residents and businesses.

In the first year as CEO, he launched a youth summer jobs program, dubbed Summer Job Connection, which placed 560 youth into paid work experience positions with 90 Hillsborough County employers.

Flanagan is a member of Tampa Mayor Jane Castor’s workforce advisory committee, the U.S. Conference of Mayors, later being elected among his peers to serve on the board of trustees.

He serves on the community impact committee with the United Way of Tampa. He also sits on the Junior Achievement board of directors, the Early Learning Coalition of Hillsborough County and One Tampa.

1. College alma mater? Gannon University in Erie, Pa. 

2. Last book you read? There’s No Such Thing as a Bad Kid, by Thaddeus Bullard.

3. Last place you vacationed? Couer D’Alane, Idaho.

4. PC or Mac? Both.

5. Guilty-pleasure food? Strawberry ice cream.

6. We’ll find you on the weekend doing?. Golfing, riding my bike with Jack, watching Jack’s baseball games, walking the dogs.

7. Biggest fear? My son not having a full and amazing life.

8. Proudest moment? The birth of my son, Jack.

9. Dream dinner companion? My dad.

10. Any pets? Stella—a boxer, and Gretta—a Boston terrier/pug mix.

11. Who did you last text? My wife, Emily.

12. What is your cellphone wallpaper image? My son listening to his Beats.

13. What do you listen to in the car? Anything and everything. I love music.

14. What is your go-to drink order? Diet Coke most of the time. Adult time? Guinness.

15. Favorite candy? Romolo’s Sponge Candy. (It’s an Erie thing.)

16. Do you suffer from Primenesia (the act of ordering from Amazon and forgetting about it)? No. Buy local!

17. Pool or beach? Pool, but I love the beach.

18. Charity you support? St. Jude’s Children’s Hospital, United Way, Junior Achievement of Tampa Bay.

19. Favorite childhood memory? The precious few moments I shared with my dad.

20. Words of advice? “The pessimist sees difficulty in every opportunity. The optimist sees opportunity in every difficulty.” — Winston Churchill

You May Also Like

20 Questions with Joe Handy

Joe Handy has more than 20 years of experience in leading cultural institutions. He joined CMA, in 2022, from the National Black MBA Association, where he served as president and chief executive officer.  In 2005, Handy joined the Georgia Aquarium’s founding team as director of visitor services and went on to serve as the Aquarium’s

20 Questions with … Jane Castor

Jane Castor is the 59th mayor of Tampa. Under this former Tampa police chief’s leadership, her administration passed the most extensive water/wastewater infrastructure plan in city history, in addition to the first budget starting in the black since the Great Recession. Her key achievements, within the past two years, also include helping secure more than

20 Questions with Alice Bessette

Alice Bessette serves as the executive director of Leadership Tampa Bay, the regional leadership program. Leadership Tampa Bay covers four counties, Hillsborough, Pinellas, Pasco and Polk. Their mission is to engage members with businesses and community leaders to enhance knowledge of regional assets and issues. The program is designed not only to identify our regional

20 Questions with Mike Nursey

Mike Nursey leads TD Bank’s Middle Market strategy across the state of Florida. The bank provides financing to companies up to $1 billion in revenue for expansion, mergers and acquisitions, leveraged finance and other growth events. Nursey, a veteran in the banking industry with 33 years of experience, has been with TD Bank since 2012.

Other Posts

20 Questions with Chris Rolle

Chris Rolle serves as executive vice president, regional president of West Florida for Seacoast Banking Corp. of Florida. The region consists of markets from Lakeland down to Naples. In this role, he leads the bank’s commercial banking growth strategy in the market. As a former executive at Synovus Bank and BB&T, Rolle has a history

20 Questions with Rhea Law

Rhea Law, the eighth president in University of South Florida history, is a fifth-generation Floridian who is passionate about the success of the state. Actively involved in corporate, public policy, civic and charitable work, Law holds top leadership positions with many Florida-based organizations. She received gubernatorial appointments to serve on the inaugural board of trustees

20 Questions with John Graydon Smith

John Graydon Smith began as president and chief executive officer of Tampa’s Museum of Science and Industry, also known as MOSI, in April 2022. He relocated to Tampa from the Reading, Pennsylvania area where, since 2010, he served as director and CEO of the Reading Public Museum, Arboretum and Neag Planetarium. Smith arrived to Reading

20 Questions with Kim Githler

Throughout her career, Kim Githler has been an entrepreneur creating several enterprises. She was part of the ownership group of the Hyatt Regency Sarasota that renovated the 297-room property, added an 11,000 square foot ballroom and then sold it to Blackstone in 2007. While owning the Hyatt, she and her partners developed the 44-unit luxury